Sodium Carbonate → ({2-Methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}butyl)oxy]phenyl}oxy)acetic acid

HRID 1391814Notes

Reaction equation

HRID 1391814 reaction equation
Br[C:2]1[N:7]=[C:6]([CH:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([O:23]CC)=[O:22])=[C:15]([CH3:26])[CH:14]=2)[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][CH:3]=1.C1([C:33]2[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[CH:35][C:34]=2B(O)O)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][C:15]1[CH:14]=[C:13]([O:12][CH:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:34]3[CH:33]=[CH:38][C:37]([C:39]([F:42])([F:41])[F:40])=[CH:36][CH:35]=3)[N:7]=2)[CH2:9][CH2:10][CH3:11])[CH:18]=[CH:17][C:16]=1[O:19][CH2:20][C:21]([OH:23])=[O:22]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 58629817Ethyl [(4-{[1-(6-bromo-2-pyridinyl)butyl]oxy}-2-methylphenyl)oxy]acetateHCID 69207925[2-Phenyl-4-(trifluoromethyl)phenyl]boronic acid

Product 1

HCID 10366937({2-Methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}butyl)oxy]phenyl}oxy)acetic acidYield 21.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred solution of ethyl [(4-{[1-(6-bromo-2-pyridinyl)butyl]oxy}-2-methylphenyl)oxy]acetate (50 mg, 0.12 mmol) in DME (0.5 mL) was treated with phenyl 4-(triflouromethyl)benzeneboronic acid (23 mg, 0.12 mmol) followed by Pd(PPh3)4 (14 mg, 0.01 mmol) and a solution of Na2CO3 (38 mg, 0.36 mmol) in water (0.5 mL), and the resulting mixture was heated at 70° C. for 18 hours under nitrogen. The solvent was then removed under vacuum and the resulting mixture acidified with aqueous HCl (2M) and then partitioned between water and EtOAc, the layers separated and the organic layer reduced to an oil. Purification by mass directed auto-prep HPLC afforded the title compound (12 mg).

Workup

  1. customThe solvent was then removed under vacuum
  2. custompartitioned between water and EtOAc
  3. customthe layers separated
  4. customPurification by mass

Sources & evidence

ORD record
ord-e79e50afda424ada8a54314d39c422ce
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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